(5R,8S,10S,13R,14S,17R)-3-Hydroxy-4,4,10,13,14-pentamethyl-17-[(R)-1-methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-4,5,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-2-carboxylic acid methyl ester | 861216-61-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (5R,8S,10S,13R,14S,17R)-3-Hydroxy-4,4,10,13,14-pentamethyl-17-[(R)-1-methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-4,5,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-2-carboxylic acid methyl ester
• CAS: 861216-61-7
• 化学式: C₃₅H₅₆O₅
• 分子量: 556.827
• InChiKey: VAAYCWXKEOQZQR-AFXDWHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.53
• 重原子数：
  40.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5R,8S,10S,13R,14S,17R)-3-Hydroxy-4,4,10,13,14-pentamethyl-17-[(R)-1-methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-4,5,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-2-carboxylic acid methyl ester 在 吡啶 、 苯基氯化硒 、 双氧水 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 以50%的产率得到(5R,8S,10S,13R,14S,17R)-4,4,10,13,14-Pentamethyl-17-[(R)-1-methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-3-oxo-4,5,6,7,8,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic lanostane-type triterpenoids as inhibitors of DNA topoisomerase II

  摘要：

  DNA topoisomerase (Topo) II is one of the target enzymes for chemotherapeutic drug development. Lanostane-type triterpenoids with various functional groups (-Cl, -Br, -OMe, -CHO, -CN, -COOH, and -COOMe) at C-2 were synthesized from 3-oxolanost-9(II)-en-24S,25-diol (9) isolated from Pinus luchuensis and their inhibitory effects on Topo II activity and cytotoxic activities against A549 cells were examined. All the derivatives showed Topo II inhibitory effects with IC50 values ranging from 1.86 to 149.97 mu M and cytotoxic activities with ED50 values ranging from 3.96 to 38.15 mu M. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.052
• 作为产物：
  描述：

  3-oxolanost-9(11)-ene-24S,25-diol 在 对甲苯磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (5R,8S,10S,13R,14S,17R)-3-Hydroxy-4,4,10,13,14-pentamethyl-17-[(R)-1-methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-propyl]-4,5,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthetic lanostane-type triterpenoids as inhibitors of DNA topoisomerase II

  摘要：

  DNA topoisomerase (Topo) II is one of the target enzymes for chemotherapeutic drug development. Lanostane-type triterpenoids with various functional groups (-Cl, -Br, -OMe, -CHO, -CN, -COOH, and -COOMe) at C-2 were synthesized from 3-oxolanost-9(II)-en-24S,25-diol (9) isolated from Pinus luchuensis and their inhibitory effects on Topo II activity and cytotoxic activities against A549 cells were examined. All the derivatives showed Topo II inhibitory effects with IC50 values ranging from 1.86 to 149.97 mu M and cytotoxic activities with ED50 values ranging from 3.96 to 38.15 mu M. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.052